Man from Dating Site Brought His Parents on Our First Date with Their Ridiculous Demand – I Decided to Outplay Them

Who brings their parents to a first date? My boyfriend from a dating app did. But what really got me was the list of OUTRAGEOUS DEMANDS his parents brought with them. I knew I’d have to outwit them… but on my own terms.

When I virtually met Jacob on a dating site several months ago, we hit it off instantly. The connection felt real — the kind that makes your heart skip a beat when you see a new message notification. I grew to think that he was “the one,” but then when we actually met… well, let’s just say reality has a way of shattering our perfectly crafted illusions.

A woman holding a phone | Source: Unsplash

A woman holding a phone | Source: Unsplash

Three months of late-night texts and hour-long video calls had built up to this moment. Jacob wasn’t just another match; he was different.

While most guys led with cheesy pickup lines or bland “hey” messages, he had caught my attention with a detailed comment about my profile photo taken at Comic-Con.

“Is that a handmade Scarlet Witch costume?” he’d written. “The detail work is incredible!”

From there, our conversations flowed naturally. He listened, really listened, when I talked about my work as a graphic designer and my dreams of starting my own studio.

A woman using a computer | Source: Midjourney

A woman using a computer | Source: Midjourney

He shared my love for true crime podcasts and could quote every episode of my favorite shows by heart. When I mentioned my sister’s battle with depression, he opened up about his own experiences with anxiety.

“I feel like I can tell you anything,” he’d said during one of our video calls, his warm brown eyes crinkling at the corners. “I’ve never connected with someone like this before.”

“Me neither,” I’d admitted, feeling my cheeks flush. “Sometimes I worry this is too good to be true.”

He’d laughed then, running a hand through his dark hair. “I can’t wait to finally meet you in person. Friday at Coffee Beanz? 7 p.m.?”

A man using a laptop | Source: Pexels

A man using a laptop | Source: Pexels

“It’s a date! Finally!” I’d chirped, unable to contain my excitement.

“See you on Friday!” He said as I hung up, blushing.

I spent the entire week planning my outfit, finally settling on a gorgeous dress that my best friend Sarah insisted brought out my eyes.

“He won’t know what hit him,” she’d said, helping me style my hair.

Friday evening found me standing outside Coffee Beanz, smoothing down my dress for the hundredth time. Through the window, I could see couples enjoying their meals, soft candlelight flickering across their faces.

People in a cafe | Source: Unsplash

People in a cafe | Source: Unsplash

My hands were shaking slightly as I pushed open the heavy wooden door, the warm aroma of garlic and fresh bread enveloping me. My eyes nervously darted around in search of Jacob.

“Lia! Over here!”

I turned toward Jacob’s familiar voice, my practiced smile freezing on my face. There he sat, but not ALONE.

An older couple sat beside him, their faces beaming with smiles. My heart, which had been filled with excitement all day, sank to my stomach.

“Hey… um, hi, what’s going on?” I managed, my brain struggling to process the scene before me.

A shocked woman | Source: Pexels

A shocked woman | Source: Pexels

Jacob stood up, his bright smile unchanged as if this was completely normal. “Lia, I’m so excited to finally meet you! These are my parents, Linda and Patrick!”

Linda, a petite woman with perfectly coiffed gray hair and gold earrings that probably cost more than my monthly rent, gave me a practiced smile that didn’t reach her eyes. Patrick, sporting a dress shirt that seemed a size too small for his frame, barely looked up from his menu.

“Sit down, girl,” Linda patted the chair next to her, not next to Jacob. “While we wait for our appetizers, I have a few questions for you.”

An older lady smiling | Source: Midjourney

An older lady smiling | Source: Midjourney

I sank into the chair, still trying to make sense of this ambush. The waiter appeared with water glasses, and I found myself wishing it was something stronger.

That’s when Linda pulled out a crisp sheet of paper from her designer handbag.

“Now then,” she cleared her throat, clicking her gold-plated pen. “I’ve prepared a brief questionnaire to help us get to know you better. I want you to fill it out.”

Sheets of paper on a table | Source: Pexels

Sheets of paper on a table | Source: Pexels

My eyes scanned the paper she placed before me, each question worse than the last:

1. What is your current annual income and five-year career projection?

2. Please list any medical conditions, including a family history of genetic disorders.

3. How many romantic partners have you had, and what were the reasons for those relationships ending?

4. Do you own or lease your vehicle? What is your credit score?

5. Are you willing to sign a prenuptial agreement?

6. Do you plan to work after having children? If so, who will provide childcare?

7. What is your stance on living with in-laws?

8. Are you willing to host special occasions like Thanksgiving & Christmas every year without expecting a penny from your partner?

A startled woman covering her mouth | Source: Pexels

A startled woman covering her mouth | Source: Pexels

The questions went on and on like a never-ending train carriage. My water glass stopped halfway to my mouth. “I’m sorry, but is this for real?”

“Of course it is, dear,” Linda replied, her tone suggesting I was being deliberately difficult. “Our family has certain standards to maintain. We need to ensure any potential partners for our Jacob are… suitable.”

My eyes darted to Jacob, waiting for him to jump in, to say this was all a joke. But he just sat there, examining his napkin as if it held the secrets of the universe.

A man sitting casually | Source: Midjourney

A man sitting casually | Source: Midjourney

Something snapped inside me. Three months of building this connection, sharing hopes and fears, only to be treated like a job applicant? No. This called for a different approach.

“Would you excuse me for just a moment?” I smiled sweetly. “Ladies’ room.”

Instead of heading to the restroom, I ducked into the convenience store next door. Five minutes later, I returned with my own notebook and pen.

“Before I answer your questions,” I said, sitting down with renewed confidence, “I have a few of my own.”

A woman holding a piece of paper | Source: Pexels

A woman holding a piece of paper | Source: Pexels

Linda’s perfectly plucked eyebrows shot up in surprise as I placed the paper with my questions on the table. She picked it up and began reading loudly, her face speaking volumes of her anger.

“Question one: At what point did you realize your son wasn’t capable of choosing his own partner?”

Patricks’s face reddened. Jacob finally looked up from his napkin.

“Question two: How many women have actually completed your interrogation process? Or do most run screaming before the credit check?”

“This is completely inappropriate!” Linda’s voice pitched higher as she continued to read.

A furious older woman with a man | Source: Midjourney

A furious older woman with a man | Source: Midjourney

“Question three: Do you also inspect their teeth like show horses, or is that saved for the second date?”

“Question four: When Jacob moves out of your basement, will you be requiring his future wife to submit weekly progress reports?”

“Question five: Have you considered therapy for your control issues, or is that too personal a question?”

“That’s enough!” Jacob slammed his hand on the table, making the silverware jump. “You have no right to disrespect my family like this!”

An angry man | Source: Midjourney

An angry man | Source: Midjourney

I leaned back, crossing my arms. “Oh, but they have every right to treat me like I’m applying for a position at the FBI?”

“My parents are just looking out for me,” he protested, his voice weak. “They want what’s best— “

“No, Jacob. What’s best for you would be growing a backbone and living your own life.”

Linda and Patrick were already gathering their things, faces flushed with indignation. Linda’s hands shook as she stuffed her questionnaire back into her bag.

“We’re leaving,” she announced. “Jacob, come on. She’s not the one for you.”

“Wait!” I called out, loud enough for nearby tables to turn. “Aren’t you forgetting something?”

Side shot of a woman | Source: Midjourney

Side shot of a woman | Source: Midjourney

They paused. “WHAT??”

“Waiter, these people are trying to leave without paying their bill!” I announced loudly, waving to the waiter. “Guess running out on checks is another proud family tradition!”

The restaurant had gone quiet. Linda’s hands shook as she pulled out her credit card, practically throwing it at the waiter. I stood up, smoothing my dress once again.

“Well, this has been entertaining. I’ll cover my water.” I placed a five-dollar bill on the table and turned to Jacob.

“Good luck finding someone who meets your family’s rigorous standards. Although, you might want to try job recruitment sites instead of dating apps. I hear they provide detailed background checks and references.”

A woman laughing | Source: Midjourney

A woman laughing | Source: Midjourney

As I walked out into the cool evening air, my phone buzzed with a message from Jacob, “You didn’t have to be so cruel. My parents were just looking out for me.”

I typed back, “Just looking out for myself, mama’s boy. Goodbye!”

Later that night, Sarah called to hear about the date. After I finished telling her everything, she was quiet for a moment.

“You know what?” she finally said. “I bet Linda has a spreadsheet ranking all of Jacob’s potential wives.”

We both burst out laughing, and I felt the last of my disappointment melt away. Dodged a bullet? Absolutely. And I’ve never been so grateful for a red flag wrapped in a questionnaire.

A woman walking away | Source: Midjourney

A woman walking away | Source: Midjourney

This work is inspired by real events and people, but it has been fictionalized for creative purposes. Names, characters, and details have been changed to protect privacy and enhance the narrative. Any resemblance to actual persons, living or dead, or actual events is purely coincidental and not intended by the author.

The author and publisher make no claims to the accuracy of events or the portrayal of characters and are not liable for any misinterpretation. This story is provided “as is,” and any opinions expressed are those of the characters and do not reflect the views of the author or publisher.

Inside the love story of Hasnat Khan and Princess Diana

Princess Diana was known for her heartfelt visits to hospitals, where she brought joy and hope to those in need.

However, one visit turned into something far more — a passionate love affair that remained shrouded in secrecy for years.

It’s 1995 – just two months prior to the infamous Panorama interview that would forever alter Diana’s life. You might remember that interview, when Princess Diana came clean about her struggles with mental health and the trials of her marriage, capturing the world’s empathy.

Two months before that interview, Diana crossed paths with a handsome doctor, a Muslim whose dark good looks were compared to the charming actor Omar Sharif.

The dashing heart surgeon, Dr. Hasnat Khan, worked at the Royal Brompton Hospital in London. But how did this unlikely pair end up together?

Diana at Royal Brompton Hospital / Getty Images

Well, that’s because Joe Toffolo, the patient who underwent surgery, was married to Oonagh Shanley-Toffolo, an Irish nun and acupuncturist who was a close confidante of Princess Diana.

After the initial visit, Diana returned to the hospital almost daily for three weeks, eager to pursue the handsome surgeon. The connection was electric.

Smoked cigarettes and loved KFC

Today, when we look back at countless photos of Diana visiting the hospital, it’s officially stated that she went to cheer up sick children or raise awareness for cystic fibrosis.

That’s definitely true. However, she also had personal reasons. Beneath the surface, her motivations were deeply personal. Because at 35, Diana had discovered a reason to smile once more.

Pakistani surgeon Hasnat Khan, identified as an “ex-lover” of Lady Diana, Princess of Wales.
(Photo by Stan Karczmarz/Sygma via Getty Images)

When Diana and Khan started seeing each other, it marked Diana’s most serious involvement since her separation from Prince Charles three years earlier.

But it came shrouded in secrecy. Few knew about their budding romance, a bond that seemed improbable at first glance. Dr. Khan, then 37, was a heart surgeon
that was running fat and smoked a pack of cigarettes a day,

He had penchant for late-night jazz clubs and Kentucky Fried Chicken — an unconventional match for the Princess of Wales.

But this didn’t stop Diana.

”He’s drop-dead gorgeous,” Diana reportedly told Oonagh Toffolo.

Secret messages

To keep their love under wraps, Diana cleverly disguised her messages for Khan, using the alias ”Dr. Armani.” They met in secret, often in unconventional spots to avoid prying eyes.

On one occasion, Diana donned a black wig to sneak into Ronnie Scott’s, a famous jazz club in Soho. In another instance, Khan hid in the boot of a car to slip into Kensington Palace, aided by Diana’s loyal butler, Paul Burrell.

Their romance flourished even during casual outings.

Diana, Princess Of Wales, arriving at The Royal Brompton Hospital, Fulham Road, London. The Princess is wearing a high-buttoning pale blue jacket designed by Versace / Tim Graham / Getty Images

One day, when Diana was feeling low, Khan whisked her away to a pub near Harefield Hospital where he had worked. The name? The Prince of Wales.

”She thought it was hilarious,” he recalled with a chuckle.

Diana was so enamored that she even asked her butler to find a priest who could marry them, despite Khan’s Muslim faith. Their love deepened as they spent time together, sharing laughter and discovering each other’s worlds.

Diana reportedly read books on Islam and cherished a photograph of “my dishy doctor.” She even visited Khan’s family in Lahore, Pakistan, where she embraced their culture and enjoyed a delightful afternoon tea.

Met William and Harry

This whirlwind romance took a more serious turn when Diana introduced Khan to her sons, William and Harry.

She described him as “Mr. Wonderful” and, according to her butler Burrell, she referred to Khan as her soulmate. Friends of Diana stated that he was ”the love of her life” and that she expressed distress when their relationship ended.

Yet, as love stories often go, their fairytale faced obstacles.

Muhammad Iqbal, Lady Diana and Jemima Michelle Khan (wife of Imran khan) and his son / Wikipedia Commons

The mounting pressure from the media began to take a toll on their relationship. While Diana was accustomed to the limelight, for Khan, the intense scrutiny was daunting.

He feared that pursuing their relationship publicly could jeopardize his career.

They discussed possible solutions, including moving to Pakistan — a plan that nearly came to fruition. Talks of relocating to Australia or South Africa were also on the table, but nothing materialized. According to The Guardian, Diana’s desire for public acknowledgment clashed with Khan’s reluctance, leading to a heartbreaking conclusion: the romance ended in July 1997.

Khan finds out about Dodi

Just a month later, tragedy struck. In the early hours of August 31, 1997, Diana died in a car crash in Paris, alongside her partner Dodi Fayed and their driver, Henri Paul.

Khan was blindsided by the news of Diana’s relationship with Dodi, discovering it only after it became public. ”When I found out, I was really mad; mad as hell,” he confessed in a 2012 interview.

Khan attended her funeral at Westminster Abbey.

Dr Hasnat Khan in 1997. (Photo by Antony Jones/UK Press via Getty Images)

The shadow of her tragic death looms over him still. “Sometimes I feel like screaming,” Khan shared, reflecting on the emotional turmoil. “There have been very bad times. I have moved on, but it keeps coming back.”

Despite the heartbreak, Khan fondly remembers Diana: ”We all have our drawbacks, but I found her a very normal person with great qualities and some personal drawbacks, like bad habits.”

Hasnat Khan today

In 2006, Khan married Hadia Sher Ali, a 28-year-old woman descended from Afghan royalty, but the couple divorced two years later.

He now lives in the UK, continuing his work as a heart surgeon and engaging in humanitarian efforts in Pakistan and Saudi Arabia.

Reflecting on his life, Khan shared: ”It is very good to be home. I am quite relieved to be home. My blood pressure is stable—I go fishing, I go for walks. It feels like a sanctuary. It’s very peaceful.”

Though the romance between Princess Diana and Dr. Hasnat Khan was short-lived, it remains an interesting chapter in her life, a testament to the complexity of love in the face of royal duty and public scrutiny.

As we remember the Princess, we celebrate not just her legacy, but also the love she shared with a man who saw her for who she truly was—a normal person with extraordinary qualities.

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